Thickening aqueous systems with alpha-olefin oxide-modified liquid polyether thickeners

ABSTRACT

New liquid thickeners for aqueous liquids are obtained by capping a liquid straight chain polyoxyalkylene compound derived from ethylene oxide or ethylene oxide and at least one other lower alkylene oxide by reacting said alkylene oxides with at least one active hydrogen-containing initiator having only one active hydrogen atom. The new thickeners are prepared at a molecular weight of about 1000 to about 25,000 utilizing an alpha-olefin oxide having a carbon chain of about 12 to about 18 aliphatic carbon atoms. Both block and heteric polyoxyalkylene compounds are useful. Alternatively, the new thickeners can be made by copolymerizing ethylene oxide or mixed lower alkylene oxides in the presence of said alpha-olefin oxide. The new thickeners exhibit an unexpected increase in viscosity in aqueous systems as compared with prior art liquid polyether thickening agents. The alpha-olefin oxide modified polyether thickening agents of the invention are useful in both water-based and water-glycol based hydraulic fluids.

This is a division of application Ser. No. 86,837, filed Oct. 22, 1979now U.S. Pat. No. 4,288,639.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to thickeners for aqueous systems based uponpolyethers of high molecular weight.

2. Prior Art

Polymeric water-soluble thickening agents are widely used for manypurposes. Commercially available polymeric thickeners differ widely inchemical composition. The diversity of available thickening agents is anindication that not all are equally useful. It is not unusual to findsome thickening agents which perform well in a certain environment andnot at all in another environment. In fact, in some uses, no onethickening agent is completely satisfactory and there is a continualneed and a continuing search for new thickening agents to satisfy manyunmet needs. For instance, various cellulose derivatives or otherwater-soluble polymers such as sodium polyacrylates, polyacrylamides,and polyethylene glycol fatty acid diesters are representativethickening agents. The polyethylene glycol fatty acid diesters arewidely used for textile printing emulsions, cosmetic emulsions, andaqueous pigment suspensions. These esters suffer from the defect thatthey are not resistant to hydrolysis in an acid or alkaline medium sothat under such conditions the thickening effect initially obtained isgradually reduced.

Polyoxyalkylene compounds, including high molecular weight materials arewell known for use as surface-active agents, as disclosed in U.S. Pat.No. 2,674,619. These compositions can be prepared at high molecularweights, for instance, up to 25,000 for use as aqueous thickeners. It isknown that liquid polyoxyalkylenes can be obtained by utilizing amixture of ethylene oxide and another lower alkylene oxide in an oxideratio of from 75 to 90 percent ethylene oxide to 10 to 25 percent otherlower alkylene oxides such as propylene oxide, as taught in U.S. Pat.No. 2,425,755. The polyethers of the prior art having high thickeningefficiency are generally those having the highest molecular weightsreasonably obtainable under commercial conditions with priceconsiderations being a limiting factor. Because high molecular weightpolyethers require a disproportionately longer processing time toproduce, it would be desirable to prepare high efficiency thickenersutilizing lower molecular weight polymers.

In U.S. Pat. No. 3,538,033, there are disclosed polyoxyalkylenederivatives of diepoxides having thickening properties. The thickenercompositions disclosed are useful for thickening aqueous systems and areprepared by reacting a diepoxide compound having at least 12 carbonatoms with an alkylene oxide adduct containing from 100 to 250 moles ofethylene oxide units.

In U.S. Pat. No. 3,829,506, there are disclosed biodegradablesurface-active agents having good foaming properties and foamstabilizing characteristics prepared by copolymerizing ethylene oxidealone or with another lower alkylene oxide and an alpha-olefin oxide inthe presence of a polyhydric alcohol. Molecular weights of 400 to 6000are claimed but there is no indication that the compositions are usefulas thickening agents for aqueous systems.

Low molecular weight polyethylene glycol diethers containing hydroxylgroups which are useful as foam inhibitors in washing, rinsing andcleaning compositions are disclosed in German Pat. No. 2,432,757. Theseare prepared by reacting a polyalkylene glycol ether containing hydroxylgroups with an alpha-olefin epoxide containing 4 to 18 carbon atoms.

In U.S. Pat. No. 3,475,499, there is disclosed the preparation ofglycols and glycol ethers by reacting with water 1,2-epoxides having 3to 30 carbon atoms. The compositions are disclosed as useful in thepreparation of detergents. High molecular weight polyether blockpolymers are disclosed in U.S. Pat. No. 3,535,307. Such compositionshave molecular weights of about 2000 to about 25,000 and are useful inthe preparation of polyurethanes.

SUMMARY OF THE INVENTION

New liquid thickeners for aqueous liquids are preferably obtained bycapping with an alpha-olefin oxide, a liquid straight-chainpolyoxyalkylene heteric or block copolymer intermediate which isprepared by reacting ethylene oxide and at least one other loweralkylene oxide having 3 to 4 carbon atoms with an activehydrogen-containing aliphatic or alkylaromatic initiator having only onehydrogen atom and about 12 to about 18 aliphatic carbon atoms. Thethickeners are prepared at a molecular weight from about 1000 to about25,000, preferably about 1000 to about 10,000. The alpha-olefin oxidehas a carbon chain of about 12 to about 18 aliphatic carbon atoms.Alternatively, the thickeners can be prepared by copolymerizing amixture of ethylene oxide and said lower alkylene oxides in the presenceof said alpha-olefin oxide. In addition, ethylene oxide homopolymerscapped with said alpha-olefin oxide are useful. The new thickenersexhibit an unexpected increased thickening efficiency in aqueous systemsas compared with prior art polyether thickeners of the same molecularweight.

DETAILED DESCRIPTION OF THE INVENTION

Polyether thickening agents having greatly improved thickeningefficiency can be obtained by modifying conventional polyetherthickening agents with an alpha-olefin oxide having about 12 to about 18aliphatic carbon atoms or mixtures thereof. It has been found thatwhether said alpha olefin oxide is incorporated in themodified-polyether by copolymerization to produce a heteric or blockpolyether or by capping an ethylene oxide homopolymer or a heteric orblock polyether, that greatly improved thickening efficiency withoutsubstantial reduction in viscosity stability under high shear conditionsresults.

It is well known that polyethers in comparison with esters ofpolyalkylene glycols, are resistant to hydrolysis under acid andalkaline conditions or under the effects of heating at elevatedtemperatures. Thus, under conditions where a thickening agent mustmaintain a substantial proportion of its thickening efficiency underconditions favoring hydrolysis of the polymer, polyether-type thickeningagents are a desirable choice. Heretofore, highly efficient polyetherthickeners for aqueous systems could be obtained only by utilizing highmolecular weight polyether polymers such as those having a molecularweight of at least 20,000 to 25,000. The modified polyethers of theinvention provide greatly increased thickening efficiency withoutsubstantial reduction in shear stability under conditions favoringhydrolysis.

The preparation of polyethers is well known in the art. Generally,polyethers are prepared utilizing a lower alkylene oxide, an activehydrogen containing compound, and an acid or basic oxyalkylationcatalyst in the presence of an inert organic solvent at elevatedtemperatures in the range of about 50° C. to 150° C. under an inert gaspressure generally from about 20 to about 100 lbs. per square inchgauge.

Any suitable prior art alkaline oxyalkylation catalyst can be used inthe practice of this invention. These include, for example, strongbases, such as sodium hydroxide, sodium methylate, potassium hydroxide,and the like; salts of strong bases with weak acids, such as sodiumacetate, sodium glycolate, and the like and quaternary ammoniumcompounds, and the like. The concentration of these catalysts in thereaction mixture is not critical and may vary from about 0.1 percent to5 percent by weight of the initiator compound.

An inert organic solvent may be utilized in the above-describedprocedures. The amount of solvent used is that which is sufficient toprovide a suitable reaction medium and is generally, on a molar basis,in excess of the total amount of the reactants. Examples of suitablesolvents include aliphatic hydrocarbons, such as hexane, heptane,isoheptane; aromatic hydrocarbons, such as benzene, toluene, xylene;chlorinated hydrocarbons, such as carbon tetrachloride, ethylenedichloride, propylene dichloride; and oxygenated hydrocarbons, such asdiethyl ether, dimethyl ether, anisole, and the like.

In accordance with this invention, a copolymer polyether polyol isprepared by mixing ethylene oxide and at least one lower alkylene oxidehaving 3 to 4 carbon atoms with an active hydrogen-containing compoundinitiator which can be an aliphatic or alkylaromatic compound havingabout 12 to about 18 aliphatic carbon atoms and one active hydrogen andfrom about 5 moles to 15 moles per mole of said initiator of analpha-olefin oxide having from about 12 to about 18 carbon atoms.Reaction is effeccted by heating said mixture to a temperature in therange of about 50° C. to 150° C., preferably from 80° C. to 130° C.under an inert gas pressure, preferably from about 30 to about 90 poundsper square inch gauge. The mixture of ethylene oxide and at least onealkylene oxide having from 3 to 4 carbon atoms is used in said mixturein an amount so that the resulting polyether product will contain atleast 10 percent, preferably about 70 percent to about 99 percent, byweight ethylene oxide residue. Said mixture is maintained at atemperature and pressure in said range for a period from about 1 to 10hours, preferably 1 to 3 hours.

Alternatively, block or heteric polymers of ethylene oxide and at leastone lower alkylene oxide having 3 to 4 carbon atoms can be prepared asintermediates by the reaction of said alkylene oxides with saidinitiator. These intermediate compounds are then capped with saidalpha-olefin epoxide to prepare the thickeners of this invention.Ethylene oxide homopolymers capped with said alpha-olefin oxide are alsouseful. If desired, a catalyst can be added to the reaction mixtureprior to the ethylene oxide addition. Alkaline catalysts such aspotassium hydroxide or acid catalysts such as boron trifluoride areuseful, as is well established in the art.

As is well known in the art, polyethers are prepared utilizing aninitiator compound which contains a reactive (or active) hydrogen atom.The term reactive hydrogen atom is well known and clearly understood bythose skilled in the art. However, to remove any possible ambiguity inthis regard, the term reactive hydrogen atom, as used herein and in theappended claims, includes any hydrogen atom fulfilling the following twoconditions:

1. It is sufficiently labile to open the epoxide ring of propyleneoxide, and

2. It reacts with methyl magnesium iodide to liberate methane in theclassical Zerewitinoff reaction (see Niederle and Niederle, Micromethodsof Quantitative Organic Analysis, p. 263, John Wiley and Sons, New YorkCity, 1946).

The reactive hydrogen atoms which will fulfill the above two conditionsare normally activated by being a member of a functional groupcontaining an oxygen atom, e.g., a hydroxyl group, a phenol group, acarboxylic acid group; a basic nitrogen atom, e.g., an amine group, ahydrazine group, an imine group, an amide group, a guanidine group, asulfonamide group, a urea group, a thiourea group; or a sulfur atom,e.g., a mercaptan, a thiophenol, a thiocarboxylic acid, hydrogensulfide. Alternatively, certain hydrogen atoms may be activated byproximity to carbonyl groups such as those found in cyanoacetic esters,acetoacetic esters, malonic esters, as is well known in the art.

Specific classes of initiator compounds which can be used in used inpreparing the polyoxyalkylene polymers of the invention includealiphatic monohydric alcohols, alkyl phenols, and aliphatic mercaptanswherein said initiator compounds contain 12 to 18 carbon atoms in thealkyl group thereof. The aliphatic monohydric alcohols include thealkane monoalcohols, alkene monoalchols, and alkyl monoalcohols.Specific examples of initiators include dodecylphenol, dodecylalcohol,dodecylcarboxlic acid, dodecylmercaptan, octadecylphenol,octadecylalcohol, octadecylcarboxylic acid, octadecylmercaptan, laurylalcohol, myristyl alcohol, and cetyl alcohol. The use ofoctadecylalcohol (stearyl alcohol) is particularly preferred. Thepreferred initiators are the aliphatic monoalcohols having a carbon atomchain length of about 12 to about 18 carbon atoms. It is preferred thatthe carbon atom chain contain about 16 to about 18 aliphatic carbonatoms. Other useful alcohols are tetradecyl alcohol and hexadecylalcohol.

The heteric or block copolymers of the invention which are capped, i.e.,copolymerized with an alpha-olefin oxide having about 12 to about 18aliphatic carbon atoms are mixtures with ethylene oxide of loweralkylene oxides having 3 to 4 carbon atoms. Generally, the proportion ofethylene oxide residue in the copolymers of the invention is at leastabout 10 percent by weight, preferably about 70 to about 99 percent byweight, and most preferably about 70 to about 90 percent by weight, ofthe mixture of ethylene oxide and the alkylene oxide having 3 to 4carbon atoms. The lower alkylene oxides referred to are 1,2-propyleneoxide and the butylene oxides such as 1,2-butylene oxide and2,3-butylene oxide and tetrahydrofuran. The proportion of lower alkyleneoxides having 3 to 4 carbon atoms utilized in combination with ethyleneoxide is generally less than 90 percent by weight of the mixed copolymerand preferably is 30 to 1 percent by weight thereof.

The alpha-olefin oxides which are utilized to modify the polyethers ofthe prior art are those oxides generally containing about 12 to about18, preferably about 14 to about 18, aliphatic carbon atoms and thecommercially available mixtures thereof. The amount of alpha-olefinoxide required to obtain the more efficient polyether thickening agentsof the invention is about 1 to about 20 percent, preferably about 1 toabout 10 percent, by weight of the total weight of the polyetherthickeners of the invention. This amount of alpha-olefin oxide basedupon the molar amount of active hydrogen-containing initiator compoundis about 5.0 mole to about 15.0 moles of alpha-olefin oxide per mole ofmonofunctional active hydrogen-containing initiator. Preferably, thealpha-olefin epoxide contains a mixture of about 14 to about 16 carbonatoms and linear alkyl chains. Examples of useful alpha-olefin oxidesare those commercially available under the trademark VIKOLOX.

Since the preparation of heteric and block copolymers of alkylene oxidesand ethylene oxide homopolymers are well known in the art, furtherdescription of the preparation of said copolymers of mixed loweralkylene oxides and ethylene oxide homopolymers is unnecessary. Furtherdetails of the preparation of heteric copolymers of lower alkylene oxidecan be obtained in U.S. Pat. No. 3,829,506, incorporated herein byreference. Further information on the preparation of block copolymers oflower alkylene oxides can be obtained in U.S. Pat. No. 3,535,307,incorporated herein by reference.

Alternatively to the use of the above-described alpha-olefin oxides tomodify high molecular weight polyether polyols, it is possible tosubstitute glycidyl ethers which can be prepared by reaction of analcohol having 12 to about 18 carbon atoms with epichlorohydrin inaccordance with the teachings of U.S. Pat. No. 4,086,279 and referencescited therein, all incorporated by reference.

The following examples will illustrate the preparation of the modifiedpolyether polyols of the invention wherein a conventional polyetherpolyol is modified with an alpha-olefin oxide to provide improvedthickening efficiency.

EXAMPLE 1 (Control or Comparative Example)

A conventional polyether derived from ethylene oxide and 1,2-propyleneoxide in the ratio of 75 percent ethylene oxide and 25 percent1,2-propylene oxide was prepared by reaction with trimethylol propane intwo stages in a stainless steel autoclave. An intermediate product wasfirst prepared by reacting a mixture of trimethylol propane, potassiumhydroxide, propylene oxide, and ethylene oxide for a period of 18 hoursat 120° C. The cooled liquid product was discharged into a glasscontainer.

The final product was prepared by reacting this intermediate productwith 1,2-propylene oxide and ethylene oxide under a nitrogen atmosphereat 115° C. for 22 hours. The reaction mixture was then cooled and theviscous liquid product transferred to a glass container. The product hada molecular weight of about 23,000.

EXAMPLE 2

In this example, a heteric copolymer of ethylene oxide and 1,2-propyleneoxide having a theoretical molecular weight of 8717 is prepared. Thisintermediate is subsequently further reacted with an alpha-olefin whichis a mixture of alpha-olefin oxides having 15 to 18 carbon atoms.

Into a stainless steel one-gallon autoclave, there was charged 972 gramsof stearyl alcohol, 89.6 grams of a 45 percent aqueous solution ofpotassium hydroxide and the mixture was heated with stirring at 115° C.at a pressure of less than 10 millimeters of mercury for 30 minutes. Thevacuum was relieved with dry nitrogen to a pressure of 5 pounds persquare inch gauge, and a mixture of 407 grams of propylene oxide and1220 grams of ethylene oxide were added over a period of 4 and 3/4 hoursat a temperature of 115° C. After addition was complete, the mixture wasstirred 70 minutes at 115° C. and cooled to 80° C. The product labeledintermediate No. 1 was thereafter discharged to a one gallon glassbottle for use in the next step.

Using the previously prepared intermediate, 476 grams of saidintermediate were charged to a one-gallon stainless steel autoclavewhich had been previously flushed with nitrogen and heated for 15minutes at a temperature of 115° C. and a pressure of 10 millimeters ofmercury. After relieving the vacuum to a pressure of 5 pounds per squareinch gauge with nitrogen, a mixture of 1303 grams of propylene oxide and3909 grams of ethylene oxide were added over a period of 14 hours at atemperature of 115° C. After the addition of these ingredients wascomplete, the mixture was stirred for a period of two hours at atemperature of 115° C. and then cooled to 80° C. The second intermediateproduct was discharged to a one-gallon bottle in a yield of 5549 gramsof liquid intermediate.

Utilizing a 2600 grams portion of the above second intermediate product,a five-liter glass vessel was charged and thereafter the vessel and itscontents were heated at a temperature of 120° C. under a nitrogenatmosphere at a pressure of 20 millimeters of mercury for a period of 30minutes. Thereafter, 76 grams of a mixture of alpha-olefin oxides having15 to 18 carbon atom chains and sold under the trademark VIKOLOX 15-18by the Viking Chemical Company was added all at once. After heating thismixture for a period of 8 hours at a temperature of 120° C. under anitrogen atmosphere at atmospheric pressure, the product was cooled to80° C. and discharged to a glass container. The product wascharacterized as a viscous brown liquid at room temperature.

EXAMPLE 3

Utilizing the same procedure and proportions as in Example 2 except that7662 grams of ethylene oxide and 2554 grams of propylene oxide wereutilized to prepare intermediate No. 1, a heteric copolymer of ethyleneoxide, and 1,2-propylene oxide was prepared which was capped with analpha-olefin oxide having 15 to 18 carbon atoms in the chain. Theproduct had a theoretical molecular weight of 10,485.

EXAMPLE 4

Utilizing the same procedure and proportions as in Example 2 except that9620 grams of ethylene oxide and 3206 grams of 1,2-propylene oxide wereutilized to prepare intermediate No. 1, a heteric copolymer was preparedof ethylene oxide and 1,2-propylene oxide capped with an alpha-olefinoxide having 15 to 18 carbon atoms in the chain. The product hadtheoretical molecular weight of 13,095.

                                      TABLE                                       __________________________________________________________________________    Aqueous Thickening Efficiency of Olefin-Capped Polyethers                                          C.sub.15 --C.sub.18 Alpha-Olefin                                                         Viscosity (SUS) at 100° F.                  Theoretical                                                                           Heteric Oxide Cap  (10% by Wt.                                                                          (7.5% by Wt.                           Example                                                                            Molecular Wt.                                                                         EP/PO Ratio                                                                           (% by Weight)                                                                            in Water)                                                                            in water)                              __________________________________________________________________________    1    25,000  75/25   None       51     41                                     2     8,717  75/25   2.9        1,320  190                                    3    10,485  75/25   2.9               98                                     4    13,095  75/25   2.0               266                                    __________________________________________________________________________

The preceding examples illustrate the various aspects of the inventionbut are not intended to limit it. Where not otherwise specifiedthroughout this specification and claims, temperatures are given indegrees centigrade and parts, percentages and proportions are by weight.

While this invention has been described with reference to certainspecific embodiments, it will be recognized by those skilled in the artthat many variations are possible without departing from the spirit andscope of the invention and it will be understood that it is intended tocover all changes and modifications of the invention disclosed hereinfor the purposes of illustration which do not constitute departures fromthe spirit and scope of the invention.

The embodiments of the invention in which an exclusive property orprivilege is claimed are defined as follows:
 1. The process ofthickening aqueous systems comprising the addition of an effectivethickening amount of a liquid polyether thickener having a molecularweight of about 1000 to about 25,000 to said aqueous systems, saidpolyether consisting of at least one of(A) polyethers prepared byreacting ethylene oxide and at least one lower alkylene oxide having 3to 4 carbon atoms with at least one monohydric alcohol active hydrogencompound initiator containing no more than one active hydrogen and about12 to about 18 aliphatic carbon atoms to prepare a heteric or blockcopolymer and further reacting said copolymer with at least onealpha-olefin oxide or aliphatic glycidyl ether each having a carbonchain length of about 12 to about 18 aliphatic carbon atoms and whereinsaid alpha-olefin oxide or aliphatic glycidyl ether is present in theamount of about 1 to about 20 percent by weight based on the totalweight of said thickener, and (B) polyethers prepared by reactingethylene oxide with at least one monohydric alcohol active hydrogencompound initiator to prepare a homopolymer and further reacting saidhomopolymer with at least one alpha-olefin oxide or aliphatic glycidylether wherein said initiator is an aliphatic or alkylaromatic compoundwhich contains no more than one active hydrogen, has a carbon chainlength of about 12 to about 18 aliphatic carbon atoms and wherein saidalpha-olefin oxide or aliphatic glycidyl ether has a carbon chain lengthof about 12 to about 18 aliphatic carbon atoms, and is present in theamount of about 1 to about 20 percent by weight based on the totalweight of said thickener.
 2. The process of claim 1 wherein saidpolyether thickening agent is the reaction product of the sequentialpolymerization of ethylene oxide and at least one of said lower alkyleneoxides to prepare an intermediate which is subsequently capped with saidalpha-olefin oxide.
 3. The process of claim 1 wherein said polyether isprepared by polymerizing a mixture of ethylene oxide and at least one ofsaid lower alkylene oxides to prepare a heteric copolymer intermediatewhich is subsequently capped with said alpha-olefin oxide.
 4. Theprocess of claim 3 wherein said ethylene oxide is present in saidpolyether in an amount of at least 10 percent by weight of the weight ofsaid polyether and said lower alkylene oxide is selected from the groupconsisting of propylene oxide, the butylene oxides, tetrahydrofuran andmixtures thereof.
 5. The process of claim 4 wherein the proportion ofsaid ethylene oxide to said lower alkylene oxide in said polyetherpolyol is in the amount of about 70 to about 99 percent by weightethylene oxide to about 30 to about 1 percent by weight of said loweralkylene oxide.
 6. The process of claim 5 wherein said monohydricalcohol initiator is an aliphatic monoalcohol selected from the groupconsisting of alkane monoalcohols, alkene monoalcohols, and alkynemonoalcohols.
 7. The process of claim 6 wherein said initiator is analkane alcohol selected from the group consisting of at least one ofstearyl alcohol, lauryl alcohol, myristyl alcohol, and cetyl alcohol. 8.The process of claim 7 wherein the mole ratio of said initiator to saidalpha-olefin oxide is 1:5 to 1:15.
 9. The process of claim 8 whereinsaid aqueous system comprises water or a mixture of water and ethyleneglycol.
 10. A composition comprising water and a polyether thickenerhaving a molecular weight of about 1000 to about 25,000 wherein saidpolyether is selected from the group consisting of at least one of(A)polyethers prepared by reacting ethylene oxide and at least one loweralkylene oxide having 3 to 4 carbon atoms with at least one monohydricalcohol active hydrogen compound initiator containing no more than oneactive hydrogen and about 12 to about 18 aliphatic carbon atoms toprepare a heteric or block copolymer and further reacting said copolymerwith at least one alpha-olefin oxide or aliphatic glycidyl ether eachhaving a carbon chain length of about 12 to about 18 aliphatic carbonatoms and wherein said alpha-olefin oxide or aliphatic glycidyl ether ispresent in the amount of about 1 to about 20 percent by weight based onthe total weight of said thickener, and (B) polyethers prepared byreacting ethylene oxide with at least one monohydric alcohol activehydrogen compound initiator to prepare a homopolymer and furtherreacting said homopolymer with at least one alpha-olefin oxide oraliphatic glycidyl ether wherein said initiator is an aliphatic oralkylaromatic compound which contains no more than one active hydrogen,has a carbon chain length of about 12 to about 18 aliphatic carbon atomsand wherein said alpha-olefin oxide or aliphatic glycidyl ether has acarbon chain length of about 12 to about 18 aliphatic carbon atoms, andis present in the amount of about 1 to about 20 percent by weight basedon the total weight of said thickener.
 11. The composition of claim 10additionally containing ethylene glycol.
 12. The composition of claim 11wherein said polyether is prepared by the heteric polymerization of amixture of ethylene oxide and propylene oxide with stearyl alcohol asinitiator to produce an intermediate heteric copolymer which issubsequently capped with said alpha-olefin oxide to produce a polyetherhaving a molecular weight of about 1000 to about 25,000.